Identification

Name
Chlorphenesin
Accession Number
DB00856  (APRD00867)
Type
Small Molecule
Groups
Approved, Vet Approved, Withdrawn
Description

A centrally acting muscle relaxant. Its mode of action is unknown. Chlorphenesin is not available in the United States.

Structure
Thumb
Synonyms
  • 3-(4-Chlorophenoxy)-1,2-propanediol
  • 3-(P-Chlorophenoxy)-1,2-propanediol
  • 3-(P-Chlorophenoxy)propane-1,2-diol
  • Chlorphenesin
  • Chlorphénésine
  • Chlorphenesinum
  • Clorfenesina
  • Glycerol alpha-P-chlorophenyl ether
  • P-Chlorophenyl-alpha-glyceryl ether
Product Ingredients
IngredientUNIICASInChI Key
Chlorphenesin carbamate57U5YI11WP886-74-8SKPLBLUECSEIFO-UHFFFAOYSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Mycil CreamCream10 mgTopicalAllen & Hanburys A Glaxo Canada Ltd. Co.1948-12-311996-09-10Canada
Mycil PowderPowder10 mgTopicalAllen & Hanburys A Glaxo Canada Ltd. Co.1951-12-311996-09-10Canada
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Mycil Cream 1%Cream1.0 %TopicalWell Spring Pharmaceutical Corporation1996-04-302004-07-19Canada
Mycil Powder 1%Powder1 %TopicalRoberts Pharmaceutical1996-07-301999-08-11Canada
International/Other Brands
Kolpicortin / Maolate (UpJohn ) / Rinlaxer
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
AnivyChlorphenesin (10 mg) + Benzocaine (10 mg) + Titanium dioxide (210 mg) + Zinc oxide (235 mg)OintmentTopicalAllen & Hanburys A Glaxo Canada Ltd. Co.1988-03-231996-09-10Canada
Categories
UNII
I670DAL4SZ
CAS number
104-29-0
Weight
Average: 202.635
Monoisotopic: 202.039671925
Chemical Formula
C9H11ClO3
InChI Key
MXOAEAUPQDYUQM-UHFFFAOYSA-N
InChI
InChI=1S/C9H11ClO3/c10-7-1-3-9(4-2-7)13-6-8(12)5-11/h1-4,8,11-12H,5-6H2
IUPAC Name
3-(4-chlorophenoxy)propane-1,2-diol
SMILES
OCC(O)COC1=CC=C(Cl)C=C1

Pharmacology

Indication

Used, along with rest and physical therapy, to treat injuries and other painful muscular conditions. Investigated for use in trigeminal neuralgia (tic douloureux), a neuropathic disorder characterized by severe facial pain. Was investigated as a modulator of histamine release.

Structured Indications
Not Available
Pharmacodynamics

Chlorphenesin is a muscle relaxant. It blocks nerve impulses (or pain sensations) that are sent to the brain.

Mechanism of action

The mechanism of action of chlorphenesin is not well defined, and its effects are measured mainly by subjective responses. It is known that chlorphenesin acts in the central nervous system (CNS) rather than directly on skeletal muscle.

Absorption

Rapid and complete.

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

Hepatic. 85% of a dose excreted within 24 hours as the glucuronide metabolite.

Route of elimination
Not Available
Half life

2.3-5 hours

Clearance
Not Available
Toxicity

Symptoms of a chlorphenesin overdose include drowsiness and nausea.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AripiprazoleThe serum concentration of Aripiprazole can be decreased when it is combined with Chlorphenesin.Approved, Investigational
SaxagliptinThe serum concentration of Saxagliptin can be decreased when it is combined with Chlorphenesin.Approved
Food Interactions
Not Available

References

Synthesis Reference

Parker, H.E.; U S . Patent 3,214,336; October 26, 1965; assigned to The Upjohn Company. Collins, R.J. and Matthews, R.J.; US. Patent 3,161,567; December 15, 1964; assigned to The Upjohn Company.

General References
  1. Malley A, Baecher L: Inhibition of histamine and SRS-A from monkey lung tissue by chlorophenesin. J Immunol. 1971 Aug;107(2):586-8. [PubMed:4105542]
  2. Kurachi M, Aihara H: Effect of a muscle relaxant, chlorphenesin carbamate, on the spinal neurons of rats. Jpn J Pharmacol. 1984 Sep;36(1):7-13. [PubMed:6503049]
  3. Dalessio DJ: Medical treatment of the major neuralgias. Semin Neurol. 1988 Dec;8(4):286-90. [PubMed:3074423]
External Links
Human Metabolome Database
HMDB14994
KEGG Compound
C07928
PubChem Compound
7697
PubChem Substance
46504714
ChemSpider
7411
ChEBI
3642
ChEMBL
CHEMBL388751
PharmGKB
PA164784022
Drugs.com
Drugs.com Drug Page
ATC Codes
D01AE07 — Chlorphenesin
MSDS
Download (35.8 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
  • Pharmacia and upjohn co
Packagers
Not Available
Dosage forms
FormRouteStrength
OintmentTopical
CreamTopical10 mg
CreamTopical1.0 %
PowderTopical10 mg
PowderTopical1 %
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)86–92Salim, E.F., Booth, R.E. (1967). "Qualitative and quantitative tests for chlorphenesin carbamate". Journal of Pharmaceutical Sciences 56 (5): 623–4. doi:10.1002/jps.2600560516. PMID 6032776.
water solubility1E+004 mg/LMERCK INDEX (1996); less than
logP1.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility10.4 mg/mLALOGPS
logP1.46ALOGPS
logP1.1ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)13.62ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.69 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity49.58 m3·mol-1ChemAxon
Polarizability20.1 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9803
Blood Brain Barrier+0.6433
Caco-2 permeable-0.5562
P-glycoprotein substrateNon-substrate0.5768
P-glycoprotein inhibitor INon-inhibitor0.8531
P-glycoprotein inhibitor IINon-inhibitor0.9212
Renal organic cation transporterNon-inhibitor0.8694
CYP450 2C9 substrateNon-substrate0.8815
CYP450 2D6 substrateNon-substrate0.8373
CYP450 3A4 substrateNon-substrate0.7335
CYP450 1A2 substrateInhibitor0.6099
CYP450 2C9 inhibitorNon-inhibitor0.9114
CYP450 2D6 inhibitorNon-inhibitor0.9292
CYP450 2C19 inhibitorNon-inhibitor0.6201
CYP450 3A4 inhibitorNon-inhibitor0.9412
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8428
Ames testNon AMES toxic0.7102
CarcinogenicityNon-carcinogens0.8053
BiodegradationNot ready biodegradable0.8233
Rat acute toxicity2.1025 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8938
hERG inhibition (predictor II)Non-inhibitor0.8296
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenol ethers
Sub Class
Not Available
Direct Parent
Phenol ethers
Alternative Parents
Phenoxy compounds / Chlorobenzenes / Alkyl aryl ethers / Aryl chlorides / Secondary alcohols / 1,2-diols / Primary alcohols / Organochlorides / Hydrocarbon derivatives
Substituents
Phenoxy compound / Phenol ether / Alkyl aryl ether / Chlorobenzene / Halobenzene / Monocyclic benzene moiety / Aryl halide / Aryl chloride / 1,2-diol / Secondary alcohol
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
propane-1,2-diols, monochlorobenzenes, glycol (CHEBI:3642)

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Not Available
Gene Name
CYP2B
Uniprot ID
Q14097
Uniprot Name
CYP2B protein
Molecular Weight
43147.81 Da
References
  1. Jarukamjorn K, Sakuma T, Nemoto N: Discriminating activation of CYP2B9 expression in male C57BL/6 mouse liver by beta-estradiol. Biochem Biophys Res Commun. 2000 Dec 9;279(1):288-92. [PubMed:11112454]
  2. Nims RW, Lubet RA, Fox SD, Jones CR, Thomas PE, Reddy AB, Kocarek TA: Comparative pharmacodynamics of CYP2B induction by DDT, DDE, and DDD in male rat liver and cultured rat hepatocytes. J Toxicol Environ Health A. 1998 Mar 27;53(6):455-77. [PubMed:9537282]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Oxygen binding
Specific Function
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name
CYP19A1
Uniprot ID
P11511
Uniprot Name
Aromatase
Molecular Weight
57882.48 Da
References
  1. Holloway AC, Stys KA, Foster WG: DDE-induced changes in aromatase activity in endometrial stromal cells in culture. Endocrine. 2005 Jun;27(1):45-50. [PubMed:16077170]
  2. Younglai EV, Holloway AC, Lim GE, Foster WG: Synergistic effects between FSH and 1,1-dichloro-2,2-bis(P-chlorophenyl)ethylene (P,P'-DDE) on human granulosa cell aromatase activity. Hum Reprod. 2004 May;19(5):1089-93. Epub 2004 Apr 7. [PubMed:15070871]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Medina-Diaz IM, Arteaga-Illan G, de Leon MB, Cisneros B, Sierra-Santoyo A, Vega L, Gonzalez FJ, Elizondo G: Pregnane X receptor-dependent induction of the CYP3A4 gene by o,p'-1,1,1,-trichloro-2,2-bis (p-chlorophenyl)ethane. Drug Metab Dispos. 2007 Jan;35(1):95-102. Epub 2006 Oct 11. [PubMed:17035600]
  2. Petersen MS, Halling J, Damkier P, Nielsen F, Grandjean P, Weihe P, Brosen K: Polychlorinated biphenyl (PCB) induction of CYP3A4 enzyme activity in healthy Faroese adults. Toxicol Appl Pharmacol. 2007 Oct 15;224(2):202-6. Epub 2007 Jul 14. [PubMed:17692354]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xanthine oxidase activity
Specific Function
Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Ha...
Gene Name
XDH
Uniprot ID
P47989
Uniprot Name
Xanthine dehydrogenase/oxidase
Molecular Weight
146422.99 Da
References
  1. Springer RH, Dimmitt MK, Novinson T, O'Brien DE, Robins RK, Simon LN, Miller JP: Synthesis and enzymic activity of some novel xanthine oxidase inhibitors. 3-Substituted 5,7-dihydroxypyrazolo(1,5-alpha)pyrimidines. J Med Chem. 1976 Feb;19(2):291-6. [PubMed:2778]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and...
Gene Name
PTGS2
Uniprot ID
P35354
Uniprot Name
Prostaglandin G/H synthase 2
Molecular Weight
68995.625 Da
References
  1. Fernandez P, Guillen MI, Gomar F, Aller E, Molina P, Alcaraz MJ: A novel cyclo-oxygenase-2 inhibitor modulates catabolic and antiinflammatory mediators in osteoarthritis. Biochem Pharmacol. 2004 Aug 1;68(3):417-21. [PubMed:15242808]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Identical protein binding
Specific Function
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name
BCHE
Uniprot ID
P06276
Uniprot Name
Cholinesterase
Molecular Weight
68417.575 Da
References
  1. Westlake GE, Bunyan PJ, Stanley PI, Walker CH: The effects of 1,1-di(p-chlorophenyl)-2-chloroethylene on plasma enzymes and blood constituents in the Japanese quail. Chem Biol Interact. 1979 May;25(2-3):197-210. [PubMed:466732]

Drug created on June 13, 2005 07:24 / Updated on November 07, 2017 01:43